Lithium Hydroxide → HCID 90415381, compound

HRID 1776778Notes

Reaction equation

HRID 1776778 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[CH:45]=[CH:44][C:10]([CH2:11][N:12]3[C:16]4[CH:17]=[CH:18][C:19]([O:21][CH2:22][C:23]5[CH:32]=[CH:31][C:30]6[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=6)[N:24]=5)=[CH:20][C:15]=4[N:14]=[C:13]3[CH2:33][C:34]3([C:39]([O:41]CC)=[O:40])[CH2:38][CH2:37][CH2:36][CH2:35]3)=[CH:9][CH:8]=2)[CH2:3][CH2:2]1.C1COCC1.[Li+].[OH-]>CO>[N:4]1([C:7]2[CH:8]=[CH:9][C:10]([CH2:11][N:12]3[C:16]4[CH:17]=[CH:18][C:19]([O:21][CH2:22][C:23]5[CH:32]=[CH:31][C:30]6[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=6)[N:24]=5)=[CH:20][C:15]=4[N:14]=[C:13]3[CH2:33][C:34]3([C:39]([OH:41])=[O:40])[CH2:38][CH2:37][CH2:36][CH2:35]3)=[CH:44][CH:45]=2)[CH2:3][CH2:2][O:1][CH2:6][CH2:5]1

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 90414283HCID 90414283, compound

Product 1

HCID 90415381HCID 90415381, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

To a 20 mL vial were added ethyl 1-((1-(4-morpholinobenzyl)-5-(quinolin-2-ylmethoxy)-1H-benzo[d]imidazol-2-yl)methyl)cyclopentanecarboxylate (28 mg, 0.046 mmol), THF (1.1 mL) and MeOH (1.1 mL) followed by LiOH (0.65 mL, 1 M). The reaction mixture was capped and heated to 80° C. for 3 h. The mixture was cooled to RT and the solvent was concentrated to dryness. Water (1 mL) and acetonitrile (1 mL) were added and the pH was adjusted to ˜5-6 using 1 M HCl and then the mixture was concentrated to dryness. The resulting residue was purified using FCC to provide the title compound. MS (ESI): mass calcd. for C35H36N4O4, 576.27; m/z found, 577.2 [M+H]+. 1H NMR (400 MHz, CDCl3) δ 8.20 (d, J=8.5, 1H), 8.11 (d, J=8.4, 1H), 7.83 (d, J=8.1, 1H), 7.77-7.72 (m, 1H), 7.69 (d, J=8.5, 1H), 7.58-7.53 (m, 1H), 7.33-7.31 (m, 1H), 7.22 (d, J=8.9, 1H), 7.10-7.05 (m, 1H), 6.97-6.93 (m, 2H), 6.85-6.80 (m, 2H), 5.43 (s, 2H), 5.22 (s, 2H), 3.86-3.81 (m, 4H), 3.14-3.09 (m, 4H), 3.05 (s, 2H), 2.41-2.33 (m, 2H), 1.75-1.66 (m, 2H), 1.47-1.39 (m, 4H).

Workup

  1. customThe reaction mixture was capped
  2. temperatureThe mixture was cooled to RT
  3. concentrationthe solvent was concentrated to dryness
  4. additionWater (1 mL) and acetonitrile (1 mL) were added
  5. concentrationthe mixture was concentrated to dryness
  6. customThe resulting residue was purified

Sources & evidence

ORD record
ord-cf3917a42b0849d495f96aecf83b5e70
Source dataset
uspto-grants-2016_02
Patent number
US09265770B2

Reaction notes

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